


Jeff Winger: Learning to Love

by wholock1860



Category: Community (TV)
Genre: M/M
Language: English
Status: In-Progress
Published: 2020-09-18
Updated: 2020-09-18
Packaged: 2021-03-07 15:54:40
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 1,934
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26520235
Author URL: https://archiveofourown.org/users/wholock1860/pseuds/wholock1860
Summary: After beginning to teach at Greendale, Jeff begins dating the Dean. How will he learn to accept commitment and unconditional love?
Relationships: Dean Craig Pelton/Jeff Winger
Comments: 2
Kudos: 9





	1. Chapter 1

Jeff walked into Greendale with a heavy sigh. How had he ended up here? All of the work he had put in at this school yet somehow he was right back in the same place he had wanted to leave so badly. Why had he even agreed to teaching here? It certainly wasn't because he wanted to. This was a favor for the Dean that is all. Just a favor until he could find a better job and get back on his feet. He walked to his classroom and slumped in his chair putting his feet up on the desk. "Hello class, I'm Professor Winger. Read chapter one or something and discuss it with your neighbor." He said pulling out his phone. That is when he noticed a familiar small frame in the doorway. "Dean dong! J-Professor Winger, I was coming to congratulate you on your first day of teaching with this very special gift basket of Greendale office supplies." Craig pulled a small basket with two pencils, an eraser, a stapler (no staples included), and a red pen. Jeff rolled his eyes and got up taking the basket putting it on his desk. Craig smiled wide and waved goodbye, giving Jeff a small shoulder touch on his way out.

The rest of the day went by with Jeff simply pretending to teach. As he was leaving he noticed Craig filling out papers in his office. Against his better judgement Jeff walked over and greeted the very stressed looking man. "Jeffery! Why are you here so late?" Craig asked looking up from his papers. "Is this another one of /those/ dreams?" Jeff rolled his eyes. "No it's not. I was walking by and saw you working. I've never seen you working this much. " The dean sighed "Well if you must know, due to some very poor judgement by a certain administration club, the school is now caught in an insurance scam. I've been working on getting us out of it for hours." Jeff sighed and placed his hand on his forehead. Why was he doing this? He should just walk away and go home. Instead, however he took a seat across from Craig's desk and grabbed a paper. "Ill help." Craig looked up in surprise, looking completely smitten. "Oh thank you Jeffery!"

After a few hours the two were able to figure out how to fix the issue. Jeff also ended up driving Craig home. As they were leaving Craig's car began to stall and completely broken down. Jeff had offered to drive him home convincing himself it was only because the man was his neighbor. It was in no way because Jeff actually enjoyed hanging out with him...No absolutely not. As they walked in Jeff immediately went into his apartment leaning against the door. He let out a deep breath. Teaching here was going to be one hell of a challenge.


	2. Chapter 2

Greendale ran smoothly…well as smoothly as anything could run at Greendale. Jeff eventually fell into a nice routine. He would wake up, go for a jog, do more workouts once he was home, get ready for work, go to Greendale, put out whatever fire the dean had started that day, and finally return home and drink scotch while watching soccer. However, one day his entire schedule was thrown off.   
Today he woke up at around two in the morning to a scratching at his door. He sighed and got up to see what it was. Looking through the peep hole he was shocked to see Craig drunk and disheveled crying while trying to unlock Jeff’s door. He opened it and looked at the small crying man, eyeliner streaking down his face. “Oh, sorry I thought this was my door.” He slurred stumbling over to his own door and attempting to put the key in the lock.

Jeff grew a bit worried; he had never known Craig to get drunk, let alone Craig hadn’t even hit on him. Something bad had happened and Jeff was determined to get to the bottom of it. “Hey, Craig what’s going on? How much did you have to drink?” He walked over hesitantly placing a hand on his shoulder. Craig shook off his hand “Please Jeffery, don’t tease me…Not tonight.” He said quietly. Jeff looked at him shaking his head. “I’m not trying to tease you. What happened? Are you okay?”

Suddenly without warning Craig began to sob, collapsing against Jeff as he did. “Why am I so unlikable?” He sobbed into the other man’s chest. Jeff was stunned for a moment before he came to his senses and gently wrapped his arms around Craig. “Whoa, you aren’t unlikable. I like you.” Craig pulled away. “No Jeffery, you don’t, not the way that I like you. No one will ever like me that way. I thought I had found someone but…It turns out he didn’t like me as much as I had thought.”

Jeff frowned “Wait you had boyfriend?” Craig sighed and looked away. “Yes I /did/. “He said feeling a few more tears slip from his eyes. “But tonight, I was told that he was only dating me because he wanted to experience a gay relationship and now he knows he’s not into dudes and I guess I’m just supposed to move on after wasting two months of my life.” Craig began rambling before stopping himself, taking a shaky breath. “I decided to go to a bar and I just…drank until I stopped feeling hurt.”

Jeff pulled Craig into a hug again. “I’m sorry Craig that’s horrible. You don’t deserve to go through that. You deserve someone that will treat you right.” Jeff said as Craig cried against his chest. He wasn’t sure if it was the fact that Craig looked so vulnerable or the fact that he was tired, but the next part of his speech surprised even himself. “You may think that I don’t like you Craig but that’s only because I’m scared. I’ve never had feeling as real as the ones that I have for you. I really like you Craig. “

Craig was shocked he pulled back and looked Jeff in the eyes looking for a lie. When he found none, he bit his lip feeling more tears threaten to fall. “Y-You like me?” He whispered Jeff took a step closer placing a hand on Craig's hip. “I do” he said slowly leaning down closing his eyes. Their lips connected in which Craig could only describe as the most electrifying kiss ever. When they parted he was leaning against Jeff for support. The shock of kissing his crush made his knees go weak. Jeff smiled slightly holding him up. “If it’s okay with you I would like to take you out, maybe tomorrow at six?” He asked a bit shyly. The dean smiles wide “That would be wonderful.”


	3. Chapter 3

Today was the day…His date with Craig. Jeff was currently getting ready, fixing his hair in the mirror. Taking a deep breath, he put all of his products back in the safe where they belong. He took one more look in the mirror before walking over to his front door. There was nothing to be nervous about, Craig had been infatuated with him since he walked into the building for fucks sake, there was no way that he could mess this up. Yet somehow, he still felt a pit in his stomach as he opened the door and knocked on Craig’s. 

The dean had been freaking out all day. He was in the process of calming himself down when there was a knock on his door. He got up off of the couch and answered finding an incredibly handsome looking Jeff standing at his door. “Hello Jeffery.” He greeted blushing as his eyes trailed down the fit man’s body, looking at his toned biceps under the tight light blue shirt. Jeff smiled looking at Craig. He was dressed in a white dress shirt with black slacks and shoes. He had toned down his usual wardrobe for Jeff’s sake. Jeff presented his arm with a nervous smile. “Shall we?” he asked. Craig took his arm and the two began to walk to the elevator. As they were walking Jeff looked over with a fond smirk. “I was thinking we could go to the mall and grab some froyo.”

Craig nodded and smiled wide but as he thought his smile fell. “I adore froyo but aren’t you afraid one of your friends will see us? I know you want to keep this on the dean-low.” Jeff thought for a moment, yes it was true that he hadn’t told anyone about his bisexual tendencies yet, but he really wanted Craig to have a good time. After careful consideration and an internal panic from Craig Jeff finally decided. “I do admit that I’d prefer them not to see us, but they will need to find out eventually. Plus, I don’t want to be like the last asshole you ended up with…I’m not usually this disgustingly sappy but I know that you deserve to be happy.”

Craig could have fainted as Jeff said that. He wrapped his arms tightly around Jeff’s waist hugging him much to Jeff’s surprise. “You are so sweet Jeffery!” Jeff laughed a bit and wrapped his arms around Craig. “Yeah, but don’t tell anyone.” Craig looked up at him with the biggest smile. “I wouldn’t dream of it.” Once the two of them drove to the mall they walked into Yogurtsburgh. They got their yogurt and sat down at a table near the window. Craig reached across the table and grabbed Jeff’s hand. “This is a dream come true.” He said. Jeff gave his hand a slight squeeze, he was a little nervous about being out in public on a date with another man, but this was something that he quickly got over that when he saw how happy Craig was in the moment. Since when had he gotten so sappy?

Jeff pulled up Craig's hand and gave it a soft kiss causing Craig to blush brighter red than the cherry that was in his froyo. “You look cute today, but I have to say, I was expecting you to wear something more…elaborate” Craig looked away and bit his lip “Well, I didn’t want to scare you away by dressing to outrageously.” Jeff scoffed a bit. “Craig, I’ve known you for four years now. No outfit you wear could surprise me anymore. I’ve seen you dressed as cat woman.” Craig chuckled. “I think there is still one or two outfits that you haven’t seen…. though maybe one day.” He mused thinking about Jeff seeing those outfits trailing off. Jeff smirked a bit. “Well we will see how the next date goes.”

This caused Craig to be snapped back into reality. “Next date? You really want to go on another date with me?” He was growing more and more excited. Jeff nodded. “Well yeah, I might have trouble with commitment but I’m willing to try working through it if you are willing to help me.” Craig nodded enthusiastically. “I’d do anything for you.” He suddenly pulled Jeff into a kiss. Jeff was shocked for a moment but kissed back eagerly. When they broke apart, they were both smiling wide. “It’s getting late how about we go back to mine and watch a movie?” he asked standing up. Craig stood as well and the two left.  
That night they fell asleep on Jeff’s couch snuggling. They were woken up by a text from Frankie. It read [We need to talk].


End file.
